- An efficient route to unsymmetrical bis(azolium) salts: CCC-NHC pincer ligand complex precursors
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The coupling of N-heterocyclic azoles (imidazoles, benzimidazoles, triazoles) to bromobenzenes (1,2-; 1,3-; or 1,4) in a step-wise, sequential manner was accomplished by manipulation of reaction time and stoichiometry, which provided straight-forward acce
- Box, Hannah K.,Howell, Tyler O.,Kennon, William E.,Burk, Griffin A.,Valle, Henry U.,Hollis, T. Keith
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- Imidazolium- and Triazine-Based Porous Organic Polymers for Heterogeneous Catalytic Conversion of CO2 into Cyclic Carbonates
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CO2 adsorption and concomitant catalytic conversion into useful chemicals are promising approaches to alleviate the energy crisis and effects of global warming. This is highly desirable for developing new types of heterogeneous catalytic materials containing CO2-philic groups and catalytic active sites for CO2 chemical transformation. Here, we present an imidazolium- and triazine-based porous organic polymer with counter chloride anion (IT-POP-1). The porosity and CO2 affinity of IT-POP-1 may be modulated at the molecular level through a facile anion-exchange strategy. Compared with the post-modified polymers with iodide and hexafluorophosphate anions, IT-POP-1 possesses the highest surface area and the best CO2 uptake capacity with excellent adsorption selectivity over N2. The roles of the task-specific components such as triazine, imidazolium, hydroxyl, and counter anions in CO2 absorption and catalytic performance were illustrated. IT-POP-1 exhibits the highest catalytic activity and excellent recyclability in solvent- and additive-free cycloaddition reaction of CO2 with epoxides.
- Zhong, Hong,Su, Yanqing,Chen, Xingwei,Li, Xiaoju,Wang, Ruihu
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Read Online
- Magnetic nano-Fe3O4 supported ionic liquids: A recoverable phase transfer catalyst for c-n cross coupling reaction
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Magnetic nanoparticles-supported quaternary ammonium salts were prepared and evaluated as phase transfer catalysts. Some of them exhibited good activities in CuCl-catalyzed N-arylation of aryl amines and N-heterocycles with aryl iodides in aqueous solution without any ligands. They could be readily separated from reaction solution using an external magnet and reused three times with a little loss in activity.
- Tang, Lin,Sun, Yu,Zhou, Lingyun,Shao, Taili
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Read Online
- SBA-15 Immobilized Phenanthroline-Copper(I) Complex as a Recyclable Efficient Catalyst for N-Arylation of Amides and N-H Heterocycles with Aryl Halides
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5-(N,N-bis-3-(triethoxysilyl) propyl) ureyl-1,10-phenanthroline was prepared and successively grafted onto mesoporous silica of SBA-15 to get SBA-15 anchored ligand which was then reacted with Cu(I) to get SBA-15 anchored complex as the heterogeneous copper catalyst. This catalyst was characterized by FT-IR, XRD, CHN, AAS, TGA, EDAX, BET, SEM and TEM. The activities of the catalyst were tested in C-N cross-coupling of amides and N-H heterocycle compounds with aryl halides. The catalyst showed high catalytic activities for these cross-coupling reactions providing good to excellent yields of desired products. Moreover, the catalyst can be easily recovered by simple filtration and reused several times without significant loss of its catalytic activity.
- Hosseinzadeh, Rahman,Aghili, Nora,Tajbakhsh, Mahmood
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Read Online
- 3D printing of a heterogeneous copper-based catalyst
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One of the most important environmental challenges of modern society is to develop new catalysts that make possible chemical processes with reduced environmental impact. Catalyst immobilization is an appealing strategy that, in addition to facilitating catalyst recovery, has proved to give higher catalytic performance, since the solid support usually provides chemical, thermal, and mechanical stabilization to the catalytic species. In this work Cu/Al2O3 catalytic system with a woodpile porous structure is synthesized by 3D printing and then sintered at high temperature to generate a copper-supported rigid structure with high mechanical strength, a high surface-to-volume ratio, and controlled porosity. The catalytic species (Cu) are immobilized in the Al2O3 matrix to avoid the leaching of the metal into the reaction medium. Al2O3 was selected because it is a good material to obtain a structure with high mechanical stability after high-temperature treatment. The resulting device shows high catalytic efficacy and good recyclability and did not produce leaching of copper to the reaction medium in different Ullmann reactions. Ease of preparation, excellent reactivity, recyclability, and negligible metal contamination all make the 3D printing technique a good strategy for fabricating other types of metal/oxide heterogeneous catalytic systems.
- Tubío, Carmen R.,Azuaje, Jhonny,Escalante, Luz,Coelho, Alberto,Guitián, Francisco,Sotelo, Eddy,Gil, Alvaro
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- 4,7-Dimethoxy-1,10-phenanthroline: An excellent ligand for the Cu-catalyzed N-arylation of imidazoles
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4,7-Dimethoxy-1,10-phenanthroline (L) was found to be an efficient ligand for the copper-catalyzed N-arylation of imidazole with aryl iodides and bromides under mild conditions. A variety of hindered and functionalized imidazoles and aryl halides were transformed in good to excellent yields.
- Altman, Ryan A.,Buchwald, Stephen L.
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- The Catalytic Properties of a Copper-Based Nanoscale Coordination Polymer Fabricated by a Solvent-Etching Top-Down Route
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Manipulating particle size is a powerful means of creating unprecedented applications in both inorganic and organic materials. Coordination polymers, which are emerging as a type of organic–inorganic hybrid materials, have attracted thriving interest in a variety of applications, but nanoscale coordination polymers have scarcely been touched. In this work, the pure-phase {Cu6[1,4-bis(imidazol-1-yl)butane]3I6}∞ coordination polymer with different sizes and morphologies was synthesized for the first time through a facile top-down route assisted by solvent etching. The size and morphology could be adjusted simply by varying the participating etching solvents. Our mechanistic investigations suggest that the bulk coordination polymer as a precursor in the etching solvents may experience a process of dispersion, dissolution, and recrystallization to generate the nanoscale counterpart. High catalytic activity of the nanoscale coordination polymer was observed in the N-arylation of imidazole aryl halides, and this was attributed to a high surface area and a low coordination number of unsaturated coordination sites. This simple and rapid preparation, requiring neither specialized equipment nor harsh conditions, suggests a wealth of potential for reducing the size of coordination polymers to comply with various practical applications.
- Cao, Xiaowei,Fang, Zhenlan,Huang, Wei,Ju, Qiang
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Read Online
- Mild transition-metal-free amination of fluoroarenes catalyzed by fluoride ions
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Trimethylsilyl-protected heterocycles undergo N-C bond formation with a variety of electron-deficient fluoroarenes catalyzed by fluoride ions. This reaction avoids stoichiometric amounts of base and thus makes N-arylheterocycles accessible in a very mild and transition-metal-free way.
- Dehe, Daniel,Munstein, Isabel,Reis, Andreas,Thiel, Werner R.
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Read Online
- Synthesis and characterization of nano-cellulose immobilized phenanthroline-copper (I) complex as a recyclable and efficient catalyst for preparation of diaryl ethers, N-aryl amides and N-aryl heterocycles
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Functionalized nanocellulose was prepared and employed for immobilization of phenanthroline-copper(I) complex to afford cellulose nanofibril grafted heterogeneous copper catalyst [CNF-phen-Cu(I)]. This nanocatalyst was well characterized using FT-IR, NMR, XRD, CHNS, AAS, TGA, EDX and SEM. The activities of the synthesized catalyst were examined in the synthesis of diaryl ethers via C-O cross-coupling of phenols and aryl iodides, as well as, the preparation of N-aryl amides and N-aryl heterocycles through C-N cross-coupling of amides and N-H heterocycle compounds with aryl halides. In this trend, various substrates containing electron-donating and electron-withdrawing groups were exploited to evaluate the generality of this catalytic protocol. Accordingly, the catalyst demonstrated remarkable catalytic efficiency for both C-N and C-O cross-coupling reactions, thereby resulting in good to excellent yields of the desired products. Furthermore, the recoverability experiments of the catalyst showed that it can be readily retrieved by simple filtration and successfully reused several times with negligible loss of its catalytic activity.
- Aghili, Nora,Hosseinzadeh, Rahman,Mavvaji, Mohammad
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- Immobilization of copper(II) into polyacrylonitrile fiber toward efficient and recyclable catalyst in Chan-Lam coupling reactions
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A series of polyacrylonitrile fiber (PANF)-supported copper(II) catalysts were prepared through the immobilization of Cu(II) into prolinamide-modified PANF (PANPA-2F) and subsequently used for the synthesis of diverse N-arylimidazoles from arylboronic acids and imidazole. The prepared Cu(II)@PANPA-2Fs were well characterized by mechanical strength, FT-IR, XRD, XPS and SEM. Among them, CuCl2@PANPA-2F exhibited excellent catalytic performance, and its activity was significantly affected by the Cu loading. This catalytic system also displayed good activity in the synthesis of N-arylsulfonamides from arylboronic acids and tosyl azide. It was highly efficient in gram-scale reactions and could be reused five times. The advantages of low cost, easy preparation, good durability and facile recovery make the fiber catalyst attractive.
- Zhang, Chenlu,Zhu, Hai,Gang, Kaiyue,Tao, Minli,Ma, Ning,Zhang, Wenqin
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- Core-shell Cu2S:NiS2@C hybrid nanostructure derived from a metal-organic framework with graphene oxide for photocatalytic synthesis of N-substituted derivatives
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Recently, photocatalysis has attracted considerable interest, leading to opportunities for using renewable energy sources. A Cu:Ni metal-organic framework (MOF) modified with graphene oxide (GO) was fabricated by a facile and convenient process. Subsequen
- Yusuf, Mohammad,Hira, Shamim Ahmed,Lim, Hyeonhan,Song, Sehwan,Park, Sungkyun,Park, Kang Hyun
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p. 9018 - 9027
(2021/04/16)
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- Synthesis and Physical Properties of Tunable Aryl Alkyl Ionic Liquids (TAAILs)
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Tunable aryl alkyl ionic liquids (TAAILs) based on the imidazolium cation were first reported in 2009. Since then, a series of TAAILs with different properties due to the electron-donating or -withdrawing effect of the substituents at the aryl ring has be
- Lerch, Swantje,Strassner, Thomas
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supporting information
p. 15554 - 15557
(2021/10/06)
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- L-Proline N-oxide dihydrazides as an efficient ligand for cross-coupling reactions of aryl iodides and bromides with amines and phenols
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A novel catalytic system based on L-proline N-oxide/CuI was developed and applied to the cross-coupling reactions of various N- and O- nucleophilic reagents with aryl iodides and bromides. This strategy featured in the employment of an-proline derived dihydrazides N-oxide compound as the superior supporting ligand. By using this protocol, a variety of products, including N-arylimidazoles, N-arylpyrazoles, N-arylpyrroles, N-arylamines, and aryl ethers, were synthesized with up to 99% yield.
- Ding, Zhiqiang,Nie, Nan,Chen, Tian,Meng, Lingxin,Wang, Gongshu,Chen, Zhangpei,Hu, Jianshe
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supporting information
(2020/12/21)
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- Synthesis of some new distyrylbenzene derivatives using immobilized Pd on an NHC-functionalized MIL-101(Cr) catalyst: photophysical property evaluation, DFT and TD-DFT calculations
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In this study the catalytic application of a heterogeneous Pd-catalyst system based on metal organic framework [Pd-NHC-MIL-101(Cr)] was investigated in the synthesis of distyrylbenzene derivatives using the Heck reaction. The Pd-NHC-MIL-101(Cr) catalyst s
- Niknam, Esmaeil,Mahmoodi, Ali,Panahi, Farhad,Heydari Dokoohaki, Maryam,Zolghadr, Amin Reza,Khalafi-Nezhad, Ali
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p. 12374 - 12380
(2021/04/07)
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- COMPOUND SIMULTANEOUSLY INHIBITING LSD1 AND HDAC TARGETS AND APPLICATION THEREOF
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A compound having a general structural formula as shown in Formula I: X-AB-Y (Formula I); in the above Formula I, X is selected from any one of -CO2H, -CONHZ, -CH=CH-CO2H, -CH=CH-CONHZ, wherein Z is selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted aryl, and hydroxyl; Y = -NR1R2, wherein NR1R2 is a substituted or unsubstituted 3- to 9-membered nitrogen-containing heterocycloalkyl; A and B are each independently selected from substituted or unsubstituted phenylene, substituted or unsubstituted azaphenylene. The compound or corresponding pharmaceutical salt thereof can inhibit LSD1 and HDAC target proteins at the same time, thus inhibit the proliferation of many kinds of tumor cells and have good antitumor effect.
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Paragraph 0041; 0047-0048; 0052; 0053
(2020/11/26)
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- NOVEL HETEROCYCLIC COMPOUNDS AS CDK8/19 INHIBITORS
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The present invention relates to novel compounds of formula (I): or a pharmaceutically acceptable salt or stereoisomer thereof, which exhibit the properties of a CDK 8/19 inhibitor. The invention also relates to a pharmaceutical composition containing said compounds and to the use thereof as pharmaceutical drugs for treating diseases or disorders.
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Paragraph 0262
(2020/07/07)
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- Chan-Lam cross-coupling reaction based on the Cu2S/TMEDA system
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A catalyst based on the readily available Cu2S/TMEDA system using a stable copper(I) source was developed for the Chan-Lam cross-coupling reaction. The capability of the catalyst was demonstrated with 1H-benzo[d]imidazol-2(3H)-one, 1H-benzo[d]imidazole, and 1H-imidazole together with electron-deficient, electron-rich, and sterically demanding boronic acids at room temperature in the presence of atmospheric oxygen to give the cross-coupling products in moderate to excellent yields. In addition, the coupling reaction of 1H-benzo[d]imidazole with several pinacol or neopentylglycol boronates indicated further potential of the catalyst. The reaction conditions tolerate the hydroxyl and bromo functional groups. The catalytic system also enables to synthesize the mono-N-substituted anilines from primary aliphatic amines. However, the two model compounds for the secondary and aromatic amines, piperidine and aniline, do not react. Two sterically demanding products with the restricted C–N bond rotation, synthesized by the N-arylation of 1H-benzo[d]imidazol-2(3H)-one with o-tolylboronic acid, enabled to confirm the atropisomers prepared by the Chan-Lam cross-coupling reaction. Furthermore, an example of one-pot Chan-Lam and Suzuki-Miyaura reaction has been reported.
- Janíková, Kate?ina,Jedinák, Luká?,Volná, Tereza,Canka?, Petr
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p. 606 - 617
(2018/01/01)
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- Copper immobilized at a covalent organic framework: An efficient and recyclable heterogeneous catalyst for the Chan-Lam coupling reaction of aryl boronic acids and amines
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A polyimide covalent organic framework (PI-COF) with high thermal and chemical stabilities has been readily prepared from commercially available and inexpensive reagents and was employed as an effective support for heterogeneous copper. It was demonstrated that the obtained Cu@PI-COF is a highly active heterogeneous catalyst which can effectively promote the Chan-Lam coupling reaction of aryl boronic acids and amines in an open flask without the aid of any base or additive. In addition, the catalyst could be readily recovered from the reaction mixture by simple filtration and reused for at least eight cycles without any observable change in structure and catalytic activity.
- Han, Yi,Zhang, Mo,Zhang, Ya-Qing,Zhang, Zhan-Hui
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p. 4891 - 4900
(2018/11/21)
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- Cu-doped CoFe2O4 nanoparticles as magnetically recoverable catalyst for C–N cross-coupling reaction
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A new hybrid catalyst has been developed by immobilizing copper acetate onto surface of cobalt ferrite magnetic nanoparticles bearing N–O chelating ligand. The magnetic core of the catalyst was synthesized via ultrasound assisted co-precipitation method and characterized by FT-IR, XRD, EDX, SEM, TEM, TGA and VSM analysis. The catalyst was found to be very active for C–N bond forming reaction. Coupling of amines and aryl boronic acid could be achieved in high yield in methanol in presence of triethylamine at room temperature. After completion of the reaction the catalyst could be recovered using an external magnet and reused for consecutive catalytic cycles without significant decrease in the catalytic activity.
- Dutta, Mintu Maan,Phukan, Prodeep
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- Cobalt-Catalyzed Hydroarylations and Hydroaminations of Alkenes in Tunable Aryl Alkyl Ionic Liquids
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Tunable aryl alkyl ionic liquids (TAAILs) are a promising class of imidazolium- or triazolium-based ionic liquids. Contrary to "standard" all-alkyl ionic liquids, these carry an aryl ring together with a linear or branched alkyl chain. Their application i
- Schroeter, Felix,Lerch, Swantje,Kaliner, Maria,Strassner, Thomas
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supporting information
p. 6215 - 6219
(2018/10/05)
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- Functional 1,8-naphthyridine copper(I) complex as efficient catalyst for n-arylation of imidazoles coupling reactions
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The functional 1,8-naphthyridine copper(I) complex, synthesized through a non-catalyst C(sp3)-H methylenation, catalyzes the cross-coupling reaction of aryl halides with imidazoles, by C?N bond formation. The Cu(I) complex catalyzes the reaction with a low catalyst loading (1%, molar fraction) and cheap base even under aerobic conditions. The procedure tolerates aryl halides with various functional groups (such as methyl, methoxy, acetyl, fluoro, nitrile and nitro groups) and gives the corresponding coupling products in moderate to high yields.
- Gou, Gao-Zhang,Wu, Na,Zhang, Ju-Cheng,Shi, Ling,Liu, Gui-Yang,Liu, Wei,Mang, Chao-Yong,Chi, Shao-Ming
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p. 181 - 185
(2018/02/28)
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- Salen complex of Cu(II) supported on superparamagnetic Fe3O4@SiO2 nanoparticles: an efficient and magnetically recoverable catalyst for N-arylation of imidazole with aryl halides
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Abstract: The Fe3O4@SiO2/Salen-Cu(II) nanocatalyst is reported as a thermally and air-stable, economical, and magnetically recoverable heterogeneous catalyst for the selective and efficient N-(hetero)arylation of imidazole. Only by adding a small amount of the catalyst (0.4?mol% Cu) to the reactants and heating under air, the new presented method provides a variety of functionalized and hindered N-(hetero)arylimidazoles in good to excellent yields within short reaction times. The catalyst could be easily recovered with the aid of a permanent magnet and reused up to five consecutive runs without significant loss of activity. Also, the leaching of Cu was negligible after the fifth recycle. Particularly, using either (hetero)aryl iodides or bromides as arylating agents and the need of only small amount of the magnetically recoverable heterogeneous copper-based nanocatalyst make this method low-cost, environmentally benign, and easy to use. Graphical abstract: [Figure not available: see fulltext.].
- Sardarian, Ali Reza,Zohourian-Mashmoul, Neda,Esmaeilpour, Mohsen
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p. 1101 - 1109
(2018/02/21)
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- Copper immobilized on magnetite nanoparticles coated with ascorbic acid: An efficient and reusable catalyst for C─N and C─O cross-coupling reactions
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In a continuation of using magnetic nanoparticle (MNP)-supported catalysts, ascorbic acid (readily available, very safe and with strong affinity to MNPs) was used instead of the commonly used silica layer coating. This hybrid was used for immobilizing copper nanoparticles to produce Cu/ascorbic acid@MNPs catalyst. The catalyst was characterized and used in carbon–oxygen and carbon–nitrogen (various substrates) cross-coupling reactions in aqueous media and at room temperature with excellent product yields. Furthermore, the catalyst could be quickly and completely recovered using an external magnetic field and reused for six reaction cycles without significant change in catalytic activity.
- Hajipour, Abdol R.,Check, Maryam,Khorsandi, Zahra
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- Methylene bridging 1,8-naphthyridine ligand and copper (I) complex, preparing method and application
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The invention discloses a methylene bridging 1,8-naphthyridine ligand and copper (I) complex, a preparing method and an application. The molecular formula of the methylene bridging 1,8-naphthyridine ligand and copper (I) complex is shown in the specificat
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Paragraph 0062; 0063; 0064; 0065; 0066; 0067; 0068; 0069
(2017/04/26)
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- Heterogeneous sequential N-arylation of N-heterocycles over copper anchored mesoporous silica catalyst
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N-Arylation reaction of N-heterocyclic compounds has been carried out in excellent yield using copper anchored SBA-15 catalyst. Sequential N-arylation reactions employing single catalyst under heterogeneous condition provides a straightforward access to a
- Das, Soma,Maity, Tanmoy,Koner, Subratanath
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- Identification of Noncompetitive Inhibitors of Cytosolic 5′-Nucleotidase II Using a Fragment-Based Approach
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We used a combined approach based on fragment-based drug design (FBDD) and in silico methods to design potential inhibitors of the cytosolic 5′-nucleotidase II (cN-II), which has been recognized as an important therapeutic target in hematological cancers. Two subgroups of small compounds (including adenine and biaryl moieties) were identified as cN-II binders and a fragment growing strategy guided by molecular docking was considered. Five compounds induced a strong inhibition of the 5′-nucleotidase activity in vitro, and the most potent ones were characterized as noncompetitive inhibitors. Biological evaluation in cancer cell lines showed synergic effect with selected anticancer drugs. Structural studies using X-ray crystallography lead to the identification of new binding sites for two derivatives and of a new crystal form showing important domain swapping. Altogether, the strategy developed herein allowed identifying new original noncompetitive inhibitors against cN-II that act in a synergistic manner with well-known antitumoral agents.
- Marton, Zsuzsanna,Guillon, Rémi,Krimm, Isabelle,Preeti,Rahimova, Rahila,Egron, David,Jordheim, Lars P.,Aghajari, Nushin,Dumontet, Charles,Périgaud, Christian,Lionne, Corinne,Peyrottes, Suzanne,Chaloin, Laurent
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p. 9680 - 9696
(2016/01/12)
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- C^C* cyclometalated platinum(II) NHC complexes with β-ketoimine ligands
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C^C* cyclometalated platinum(II) NHC complexes with chelating acetylacetonate ligands have been recently shown to be an interesting class of phosphorescent emitters. We sought to clarify the role of the acetylacetonate ligand by replacing one of the coord
- Tronnier, Alexander,Poethig, Alexander,Herdtweck, Eberhardt,Strassner, Thomas
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p. 898 - 908
(2014/03/21)
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- Copper complex-catalysed C-N coupling reaction of aryl iodides with nitrogen-containing heterocycles
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An efficient method for the copper-catalysed arylation of nitrogen-containing heterocycles is reported using 3-(diphenylphosphino) propanoic acid as a ligand in combination of CuCl. The C-N coupling reactions afford various N-arylated products in good to excellent yields.
- Sajadi, S. Mohammad,Maham, Mehdi
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p. 128 - 129
(2014/03/21)
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- 8-Hydroxyquinoline functionalized peg-1000 bridged Dicationic ionic liquid as a novel Ligand for copper-catalyzed n-Arylation of Imidazoles
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A novel 8-hydroxyquinoline functionalized PEG-1000 bridged dicationic ionic liquid ([HQ-PEG1000- DIL][BF4]) was synthesized and characterized. It was applied as an efficiently recyclable ligand for copper- catalyzed N-arylation of nitrogen-containing heterocycles with aryl halides. The catalytic system could be easily recovered and reused for at least five runs without obvious loss of catalytic activity.
- Wang, Ying-Lei,Luo, Jun,Liu, Zu-Liang
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p. 1007 - 1013
(2013/10/22)
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- An in situ generated CuI/metformin complex as a novel and efficient catalyst for C-N and C-O cross-coupling reactions
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An in situ generated complex of copper(I) and a biguanide, namely metformin, was found to be a highly efficient homogeneous catalyst in N/O-arylation reactions. The O-arylation of substituted phenols with various aryl iodides and bromides was also achieved using this copper catalyst to afford diaryl ethers in good to excellent yields in DMF. This heterogeneous copper catalyst also promotes the N-arylation of imidazole with a variety of aryl halides (Cl, Br, I) in acetonitrile.
- Ghorbani-Vaghei, Ramin,Hemmati, Saba,Veisi, Hojat
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p. 7095 - 7099
(2013/12/04)
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- Catalyst-free N-arylation using unactivated fluorobenzenes
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Caught in a 'SNAr'e: A one-step, high-yielding, catalyst-free method is described for N-arylation of azoles and indoles from unactivated monofluorobenzenes. This SNAr reaction tolerates a wide range of substituents and can also generate halogenated N-aryl products. The reaction can also be performed simultaneously with or subsequent to a copper- or palladium-catalyzed cross-coupling reaction in the same pot. Copyright
- Diness, Frederik,Fairlie, David P.
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supporting information; experimental part
p. 8012 - 8016
(2012/09/05)
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- Cross-coupling of phenyl halides with sodium dicyanomethanide in the presence of Tetrakis(triphenyphosphine)palladium
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1-Aromatic substituted imidazoles were synthesized by a convenient modified process. A cross-coupling reaction of phenyl halides with sodium dicyanomethanide has been achieved to produce the arylmalononitriles coupling products as zwitterionic precursors
- Wang, Jin,Shu, Cheng,Gao, Chao,Hou, Chaoqi,Peng, Bo,Wei, Wei
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p. 1325 - 1327
(2012/08/07)
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- Efficient use of a surfactant for copper-catalyzed coupling reaction of arylboronic acids with imidazoles in water
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Copper-catalyzed oxidative coupling of arylboronic acids with imidazoles in water was realized by using an amphiphilic surfactant. By choosing an appropriate surfactant, reactions of a variety of arylboronic acids proceeded smoothly under mild and base-fr
- Inamoto, Kiyofumi,Nozawa, Kanako,Kadokawa, Jun,Kondo, Yoshinori
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experimental part
p. 7794 - 7798
(2012/09/22)
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- Phosphino imidazoles and imidazolium salts for Suzuki C-C coupling reactions
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The consecutive syntheses of imidazoles 1-(4-X-C6H 4)-4,5-R2-cC3HN2 (3a, X = Br, R = H; 3b, X = I, R = Me; 3c, X = H, R = Me; 5, X = Fc, R = H; 7, X = CCFc, R = H; 9, X = C6Hsub
- Milde, Bianca,Schaarschmidt, Dieter,Rueffer, Tobias,Lang, Heinrich
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scheme or table
p. 5377 - 5390
(2012/05/20)
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- Copper-catalyzed C-N bond formation with N-heterocycles and aryl halides
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The microwave-assisted, cuprous oxide catalyzed coupling of aryl bromides and iodides with imidazole, benzimidazole, pyrazole, or triazole was found to give a wide range of N-aryl heteroaromatic products in good to high yields. Aryl dibromides undergo sel
- Boswell, Mikki G.,Yeung, Fanny G.,Wolf, Christian
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supporting information; experimental part
p. 1240 - 1244
(2012/06/04)
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- Electronic effects of para-substitution on the melting points of TAAILs
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Owing to numerous new applications, the interest in "task- specific" ionic liquids increased significantly over the last decade. But, unfortunately, the imidazolium-based ionic liquids (by far the most frequently used cations) have serious limitations whe
- Schulz, Tobias,Ahrens, Sebastian,Meyer, Dirk,Allolio, Christoph,Peritz, Anke,Strassner, Thomas
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p. 863 - 867
(2011/10/05)
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- Salts Comprising Aryl-Alkyl-Substituted Imidazolium and Triazolium Cations and the Use Thereof
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The present invention relates to salts comprising novel aryl-alkyl-substituted imidazolium and triazolium cations and arbitrary anions. The invention further relates to methods for the chemical conversion and separation of substances, comprising the salts
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Page/Page column 8-9; 11
(2011/05/08)
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- Cross-coupling reactions of aryl halides with amines, phenols, and thiols catalyzed by an N,N′-dioxide-copper(I) catalytic system
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The coupling reactions of various N, O, and S nucleophilic reagents with aryl halides have been successfully carried out under mild conditions by using a novel chiral N,N′-dioxide-copper(I) catalytic system as the catalyst. This versatile and efficient catalyst system has been demonstrated to facilitate the cross-coupling reactions of aryl halides with amines, phenols, and thiols to afford the corresponding desired products in good to excellent yields.
- Yang, Haitao,Xi, Chao,Miao, Zhiwei,Chen, Ruyu
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supporting information; experimental part
p. 3353 - 3360
(2011/08/03)
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- A versatile and efficient cu-catalyzed N-Arylation of aromatic cyclic secondary amines with aryl halides
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A copper-catalyzed coupling reaction of aryl halides with various aromatic cyclic secondary amines in DMSO has been developed efficiently. The versatile and efficient copper catalyst system is of wide-spread and practical application in cross-coupling reactions.
- Yang, Haitao,Miao, Zhiwei,Chen, Ruyu
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experimental part
p. 325 - 331
(2012/05/31)
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- Mild conditions for copper-catalyzed N-arylation of imidazoles
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An efficient copper(I) bromide catalyzed N-arylation of azoles with a variety of aromatic bromides and iodides under mild conditions is reported. This reaction displayed great functional group compatibility and excellent reactive selectivity. Georg Thieme Verlag Stuttgart.
- Chen, Huaming,Wang, Deping,Wang, Xianyang,Huang, Wenlong,Cai, Qian,Ding, Ke
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experimental part
p. 1505 - 1511
(2010/09/14)
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- CuI nanoparticles for C-N and C-O cross coupling of heterocyclic amines and phenols with chlorobenzenes
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(Chemical Equation Presented) Employing CuI nanoparticles as an efficient catalyst for the cross-coupling reactions of various N/O nucleophilic reagents with aryl chlorides could be successfully carried out under mild conditions in the absence of both the ligands and strong bases. A variety of products including N-arylimidazoles and aryl ethers were synthesized in good to excellent yields. 2009 American Chemical Society.
- Sreedhar,Arundhathi,Reddy, P. Linga,Kantam, M. Lakshmi
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supporting information; experimental part
p. 7951 - 7954
(2010/01/16)
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- Pyridine N-oxides as ligands in Cu-catalyzed Af-arylation of imidazoles in water
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N-Arylation of imidazoles with aryl halides catalyzed by a combination of copper(II) sulfate and 1,2-bis(2-pyridyl)-ethane-N,N′-dioxide in water afforded up to 95% yield.
- Liang, Lei,Li, Zhengkai,Zhou, Xiangge
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supporting information; experimental part
p. 3294 - 3297
(2009/11/30)
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- Highly functional group tolerance in copper-catalyzed N-arylation of nitrogen-containing heterocycles under mild conditions
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A copper-catalyzed process has been developed for the N-arylation reaction under very mild conditions in the absence of additional ligand. This protocol could not only tolerate an array of thermally sensitive functional groups, but also achieve high chemoselectivity.
- Zhu, Liangbo,Li, Gaocan,Luo, Liang,Guo, Peng,Lan, Jingbo,You, Jingsong
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supporting information; experimental part
p. 2200 - 2202
(2009/07/01)
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- A simple and efficient catalytic system for N-arylation of imidazoles in water
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A study was conducted to develop a simple and efficient catalytic system for N-arylation of immidazoles in water. Demonstrations revealed that the catalytic system contained a number of significant advantages. Some of these advantages included the use of water as a green solvent in place of volatile organic solvents and the catalysis was performed without an inert gas atmosphere and with low catalyst loading. Investigations revealed that the presence of catalyst and PTC were essential for the catalysis reaction. The scope of aryl halide substrates was investigated by using the catalytic system under the optimized reaction conditions. It was also demonstrated that the catalytic system tolerated a variety of functionalized aryl halides in the reaction, including nitrile, nitro, acetyl, and ether groups. The new catalytic system was applied to a variety of imidazole derivatives to expand the scope of the methodology.
- Wang, Yi,Wu, Zhiqing,Wang, Lixia,Li, Zhengkai,Zhou, Xiangge
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supporting information; experimental part
p. 8971 - 8974
(2010/04/05)
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- Facile cuI-catalyzed arylation of azoles and amides using simple enaminones as efficient ligands
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(E)-3-(Dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one was found to be an excellent ligand for copper-catalyzed N-arylation of azoles and amides with aryl halides under mild conditions. The reaction took place at 82 C in MeCN with broad functional-group compatibility. A combination of the ligand and CuI proved to be an efficient catalytic system to promote the coupling reactions of aryl halides with azoles and amides.
- Cheng, Cungui,Sun, Gonglei,Wan, Jieping,Sun, Cuirong
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experimental part
p. 2663 - 2668
(2010/01/16)
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- Copper(I) oxide catalyzed N-arylation of azoles and amines with arylboronic acid at room temperature under base-free conditions
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N-Arylation of azoles and amines with arylboronic acids was efficiently carried out with heterogeneous copper(I) oxide in methanol at room temperature under base-free conditions. The products N-arylazoles and N-arylamines were isolated in good to excellent yields. A variety of arylboronic acids and amines were converted to the corresponding N-arylazoles and N-arylamines, demonstrating the versatality of the reaction. Georg Thieme Verlag Stuttgart.
- Sreedhar, Bojja,Venkanna, Gopaladasu T.,Shiva Kumar, Kota Balaji,Balasubrahmanyam, Vura
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p. 795 - 799
(2008/09/21)
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- N,N′-(Phenylmethylene)diacetamide analogues as economical and efficient ligands in copper-catalyzed arylation of aromatic nitrogen-containing heterocycles
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N,N′-(Phenylmethylene)diacetamide analogues which were simply prepared from the condensation reaction of an aldehyde with an amide or urea were found to be efficient ligands in copper-catalyzed coupling reaction of aryl halides with various azole nucleophiles. The newly developed ligand showed broad application scope in this conversion. Compounds including imidazoles, benzoimidazoles, pyrrole, indole, and benzotriazole were successfully arylated with diversified aromatic halides to give corresponding products in moderate to excellent yields. Georg Thieme Verlag Stuttgart.
- Wan, Jie-Ping,Chai, Yun-Feng,Wu, Jian-Mei,Pan, Yuan-Jiang
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experimental part
p. 3068 - 3072
(2009/06/28)
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- Copper-catalyzed N-arylation of imidazoles and benzimidazoles
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(Chemical Equation Presented) 4,7-Dimethoxy-1,10-phenanthroline (L1c) was found to be an efficient ligand for the copper-catalyzed N-arylation of imidazoles and benzimidazoles with both aryl iodides and bromides under mild conditions. Further optimization of the system has revealed that the addition of poly(ethylene glycol) accelerates this reaction. A variety of hindered and functionalized imidazoles, benzimidazoles, and aryl halides were transformed in good to excellent yields. Heteroaryl halides were also coupled in moderate to good yields. We also present the results obtained from a series of coupling reactions, which directly compare the use of L1c with other recently reported ligands.
- Altman, Ryan A.,Koval, Erica D.,Buchwald, Stephen L.
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p. 6190 - 6199
(2008/02/10)
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- Benzotriazole: an excellent ligand for Cu-catalyzed N-arylation of imidazoles with aryl and heteroaryl halides
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Benzotriazole (BtH) is an efficient ligand for the Cu-catalyzed N-arylation of imidazoles with aryl and heteroaryl halides. A combination of CuI/BtH was found to be an efficient and inexpensive catalyst system to carry out the N-arylation of imidazoles affording the corresponding products in good to excellent yields.
- Verma, Akhilesh Kumar,Singh, Jaspal,Sankar, V. Kasi,Chaudhary, Ritu,Chandra, Ramesh
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p. 4207 - 4210
(2008/02/05)
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- Highly efficient copper-catalyzed N-arylation of nitrogen-containing heterocycles with aryl and heteroaryl halides
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(Chemical Equation Presented) New (S)-pyrrolidinylmethylimidazole ligands (4a-c) have been readily synthesized in a straightforward fashion from least expensive starting materials in short steps in high yields. Relatively mild and highly efficient Cul-catalyzed N-arylation procedures for imidazoles with aryl and heteroaryl bromides or chlorides have been developed in the presence of 4a and Cs2CO3. It is important to note that the protocol could tolerate functional groups such as ester, nitrile, nitro, ketone, free hydroxyl, and free primary amine on the aryl halide. The protocol could also be applicable to other π-electron-rich nitrogen heterocycles (pyrrole, pyrazole, indole, benzimidazole, and triazole), affording the N-arylazoles in good to excellent yields.
- Zhu, Liangbo,Cheng, Liang,Zhang, Yuxi,Xie, Rugang,You, Jingsong
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p. 2737 - 2743
(2008/02/05)
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- A versatile and efficient ligand for copper-catalyzed formation of C-N, C-O, and P-C bonds: Pyrrolidine-2-phosphonic acid phenyl monoester
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A new and readily available bidentate ligand, namely, pyrrolidine-2- phosphonic acid phenyl monoester (PPAPM), has been developed for the copper-catalyzed formation of C-N, C-O, and P-C bonds, and various N-, O-, and P-arylation products were synthesized in good to excellent yields by using the CuI/PPAPM catalyst system. Addition of the PPAPM ligand greatly increases the reactivity of the copper catalyst, and the resulting versatile and efficient catalyst system is of widespread and practical application in cross-coupling reactions.
- Rao, Honghua,Jin, Ying,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
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p. 3636 - 3646
(2008/02/03)
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